148440-81-7

148440-81-7 structure

Name: Thioperamide (maleate)
Chemical Name: Thioperamide maleate salt
CAS Number: 148440-81-7
Molecular Formula: C₁₉H₂₈N₄O₄S
Molecular Weight: 408.515
Catalog: Signaling Pathways GPCR/G Protein Histamine Receptor
Create Date: 2018-07-08 18:15:39
Modify Date: 2024-01-13 19:24:22
Thioperamide maleate (MR-12842 maleate) is a potent, orally available, brain penetrant and selective H3 receptor antagonist with a Ki of 4.3 nM for inhibition of [3H]histamine release. Thioperamide maleate inhibits [3H]histamine synthesis with a Ki of 31 nM[1].

Name	Thioperamide maleate salt
Synonyms	MR-12842 N-Cyclohexyl-4-(1H-imidazol-4-yl)-1-piperidinecarbothioamide maleate salt 1-Piperidinecarbothioamide, N-cyclohexyl-4-(1H-imidazol-5-yl)-, (2Z)-2-butenedioate (1:1) MR-12842 (N-Cyclohexyl-4-(1H-imidazol-4-yl)-1-piperidinecarbothioamide maleate salt Thioperamide Maleate N-Cyclohexyl-4-(1H-imidazol-5-yl)-1-piperidinecarbothioamide (2Z)-2-butenedioate (1:1) 1-Piperidinecarbothioamide, N-cyclohexyl-4-(1H-imidazol-4-yl)-, (2Z)-2-butenedioate (1:1) MFCD00083209 N-Cyclohexyl-4-(1H-imidazol-4-yl)piperidine-1-carbothioamide (2Z)-but-2-enedioate (1:1)

Description	Thioperamide maleate (MR-12842 maleate) is a potent, orally available, brain penetrant and selective H3 receptor antagonist with a Ki of 4.3 nM for inhibition of [3H]histamine release. Thioperamide maleate inhibits [3H]histamine synthesis with a Ki of 31 nM[1].
Related Catalog	Signaling Pathways >> Immunology/Inflammation >> Histamine Receptor Research Areas >> Neurological Disease Signaling Pathways >> GPCR/G Protein >> Histamine Receptor
Target	H3 Receptor
In Vitro	Thioperamide inhibits [3H]-(R)α-MeHA binding rat brain and guinea-pig lung with Kis of 2.1 nM and 2.0 nM, respectively. Thioperamide competitively blocks H3-autoreceptors regulating [3H]histamine release with a mean apparent Ki of 4 nM[1]. Thioperamide (0.01-100 μM; 24 hours) promotes the viability of NE-4C stem cells in a concentration-dependent manner[2]. Thioperamide displays similar potencies at human H4 and H3 receptors (Ki=43 and 60 nM, respectively)[3]. Cell Viability Assay[2] Cell Line: NE-4C stem cells Concentration: 0.01, 0.1, 1, 10, 100 μM Incubation Time: 24 hours Result: The viability of NE-4C stem cells increased significantly to 150.83±6.91% when (1 μM) was administrated, and increased to 145.11±14.52% and 132.02%±25.65% when 10 μM and 100 μM were administrated respectively.
In Vivo	Thioperamide (5-20 mg/kg; i.p.) is able to facilitate reconsolidation of a contextually-conditioned fear memory in C57BL/6J mice[4]. Animal Model: Naive female C57BL/6J mice[4] Dosage: 5, 10 or 20 mg/kg Administration: Injections (i.p.) Result: Facilitated reconsolidation of a contextually-conditioned fear memory.
References	[1]. J M Arrang, et al. Highly Potent and Selective Ligands for Histamine H3-receptors. Nature. 1987 May 14-20;327(6118):117-23. [2]. Na Wang, et al. Histamine H3 Receptor Antagonist Enhances Neurogenesis and Improves Chronic Cerebral Hypoperfusion-Induced Cognitive Impairments. Front Pharmacol. 2020 Jan 21;10:1583. [3]. Y Charlier, et al. Differential Effects of Histamine H(3) Receptor Inverse Agonist Thioperamide, Given Alone or in Combination With the N-methyl-d-aspartate Receptor Antagonist Dizocilpine, on Reconsolidation and Consolidation of a Contextual Fear Memory in Mice. Neuroscience. 2011 Oct 13;193:132-42. [4]. Gbahou F, et al. Compared pharmacology of human histamine H3 and H4 receptors: structure-activity relationships of histamine derivatives. Br J Pharmacol. 2006;147(7):744-754.

Molecular Formula	C₁₉H₂₈N₄O₄S
Molecular Weight	408.515
Exact Mass	408.183136
PSA	150.64000
LogP	2.83690

Symbol	GHS07
Signal Word	Warning
Hazard Statements	H315-H319-H335
Precautionary Statements	P261-P305 + P351 + P338
Personal Protective Equipment	dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes	Xi
Risk Phrases	R36/37/38
Safety Phrases	S26
RIDADR	NONH for all modes of transport

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